Methanol → HCID 20296598, compound

HRID 1389479Notes

Reaction equation

HRID 1389479 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][NH:3][C:2]1=[O:11].[C:12]1([O:22][CH2:23][CH:24]2[O:26][CH2:25]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.CO>C1(C)C=CC=CC=1>[C:12]1([O:22][CH2:23][CH:24]([OH:26])[CH2:25][N:8]2[CH2:7][CH2:6][C:5]3([O:1][C:2](=[O:11])[NH:3][CH2:4]3)[CH2:10][CH2:9]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 915212-((1-Naphthalenyloxy)methyl)oxiraneHCID 129541141-Oxa-3,8-diazaspiro(4.5)decan 2-one

Product 1

HCID 20296598HCID 20296598, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2 g 1-oxa-3,8-diazaspiro[4.5]-decan 2-one, 3.12 g 2,3-epoxypropyl 1-naphthyl ether, 5 ml methanol and 10 ml toluene is heated at reflux for 5 hours. The solvent is removed by evaporation in vacuum. The residue is filtered through 20 g silica gel with 5% methanol/methylene chloride. Evaporation of solvent and recrystalization from ethyl acetate affords 3.35 g 8-[3-(1-naphthyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one, mp 178°-179°.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent is removed by evaporation in vacuum
  4. filtrationThe residue is filtered through 20 g silica gel with 5% methanol/methylene chloride
  5. customEvaporation of solvent and recrystalization from ethyl acetate

Sources & evidence

ORD record
ord-28a56cb1a607482798621afa1bd1b3d2
Source dataset
uspto-grants-1981_01
Patent number
US04244961

Reaction notes

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